My CPA requires Quickbooks online and it seems there isn’t an easy way to do the data entry and allocations and keep those two systems inline with all the transactions.  

Perform the same task in each app to ensure a fair comparison.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.Run a credit/screening report on yourself.Enter a maintenance request, assign a vendor, and attach a fake invoice.Enter charges to the tenant's ledger.Enter recurring charges and automatic late fees.Sign documents electronically.Run owner reports.After testing a few apps, one should clearly stand out.

Did it make real estate investing more easy or hard?

It won't be easy at first and once you master that one, get really good on your 2nd, 3rd, etc.

It's easy to obtain, costs very little, and doesn't require extra, on-going effort to maintain.

The area looks to be a decent area for STR rentals and has potential to be a great investment if that goes well, we won't have a mortgage on the property so outside of taxes/insurance/utilities it should be easy to cash flow.

They're pretty easy, and honestly even easier than LTR acquisitions since you are not reliant on the appraised market rent (when using AirDNA to qualify). 

It sounds like you all had it pretty easy with Milton. 

A link to FilePlace is at the bottom of every page, so it is easy to find.If you have technical issues, send an email to [email protected] and someone will help you.

It's NOT for the novice, it is unique, and very easy to loose a lot of $ first if jumping in blind.